A calixarene compound is a cyclic oligomer generally obtained by condensation of a phenol compound (e.g. phenol, resorcinol) and an aldehyde compound. In recent years, the calixarene compound is gaining attention as the third inclusion compound next to crown ether and cyclodextrin in the field of host-guest chemistry.
The calixarene compound is regarded as an outstanding functional material due to the possession of many hydroxyl groups in the molecule, excellent thermal stability, high glass transition temperature and high melting point, and film-formability according to the structure. For example, application to an electron-beam negative-tone photo resist using p-methylcalix[6]arene hexa-acetate (e.g. See Non-Patent Document 1) and application to a negative-tone alkali development-type resist containing calix[4]resorcin arene, a crosslinking agent, and a photoacid generator (e.g. See Non-Patent Document 2) have been reported. Moreover, synthesis of calixarene derivatives by the introduction of radically polymerizable functional groups and cationically polymerizable functional groups for the purpose of applying the calixarene compound to a high performance photocurable material and the introduction of protective groups for the purpose of application to a high resolution resist material, as well as the evaluation of photo-reactivity of the calixarene derivatives have been reported (e.g. See Non-Patent Document 3 to 5). Synthesis of p-alkylcalix[n]arene derivatives having various cationically-polymerizable functional groups and studies on the cationic photopolymerization of such derivatives have been reported (e.g. See Non-Patent Document 6).
In addition, among the calixarene compounds, various studies have been undertaken on calixresorcinolarene compounds which are the condensates of a resorcinol compound and an aldehyde compound regarding their capability of including large guest compounds. A number of derivatives having large and deep holes have been synthesized by chemical modification of the resorcinol ring.
For example, a basket-type cavitand with a firmly fixed cone conformation can be obtained by crosslinking hydroxyl group pairs of adjacent resorcinol rings via a covalent bond. Alkylation using a dihalomethane (See Non-Patent Document 7) and silylation using a dialkyl dichlorosilane (See Non-Patent Document 8) have been reported. As resorcinol compounds, derivatives having a functional group such as CHO (See Non-Patent Document 9), OH (See Non-Patent Document 10) or CO2R (See Non-Patent Document 11) have been reported. Furthermore, possibility of obtaining a capsule-type carcerand in which two or more cavitants having suitable functional groups are combined via an SN2 reaction has also been reported (See Non-Patent Document 12). However, since there are no more reactive groups left in these cavitants, further chemical modification of these cavitants is difficult.
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